Mike Gregg’s investment philosophy centres on building deep, long-term relationships with exceptional founders. It is an approach shaped by decades of experience, both as an operator and as an investor, and reflects a consistent belief in backing people early and staying with them over time.
In this piece published by The Australian, journalist Stephen Kanavoutsos sat down with Mike to hear the story of his journey as an early personal investor in WiseTech Global. This is a 20-year investment that has shaped how Mike thinks about conviction, patience, and what it really means to back a founder for the long haul.
By Stephen Kanavoutsos
Note: This article was published in the print edition of The Australian. No online link is available.
For more than two decades, Mike Gregg has held the same investment, a journey as a WiseTech shareholder that “has been fruitful and a hell of a lot of fun”.
Gregg first backed WiseTech Global at a moment of transition in his own career, just after exiting Health Communication Network, the healthcare software business he helped build into a dominant platform used by most Australian GPs and hospitals. HCN had grown out of a management buyout of a government operation, scaled through acquisitions, and eventually listed on the ASX.
While it was “nice to be acquired and get a cheque, I felt that I left something on the table and was determined not to let that happen a second time”, Gregg says.
What followed was immediate. “The day I left HCN, I had my second meeting with Richard White, it was a lucky set of circumstances which saw us introduced to Richard,” Gregg explains.
The question he and fellow investor Charles Gibbon were trying to answer was simple: “Can this founder scale?” Gregg and Gibbon’s assessment would ultimately be validated, with WiseTech shares reaching $135 at their peak in late 2024.
At the time, WiseTech looked like a familiar type of opportunity. “A classic software start-up story, a ‘boring’ industry transformed and made more efficient with software.”
What stood out to Gregg was the trajectory and intent. White had already taken the business from “a few people in a garage to 100-plus people”, and had a clear ambition “to use an Australian piece of software and go global”.
Gregg made a deliberate call. He and wife Sue decided he would “take half of what they made from HCN and put it to use from what I’ve learned”, deploying capital from HCN into WiseTech and other start-ups, including Shearwater Capital managing partner Zac Zavos’s start-up.
The approach was straightforward; “we made it simple” by backing WiseTech through ordinary shares and committing to the long term.
Conviction followed and compounded, with Gregg highlighting that “every board meeting increased my conviction”. Over time, the investment has become, in his words, “the best experience of my business life”.
Gregg still holds WiseTech shares, and only stepped off the board as recently as November 2025. The company’s share price has come under pressure following founder White’s personal and professional crisis.
White was accused of trading sex for investment advice, he conducted relationships with an employee and a supplier that gave rise to formal complaints from those women, and was accused of bullying a former director.
An independent review found he misled the board about a relationship with an employee, and a board subcommittee, including Gregg, acknowledged “legitimate governance concerns raised in the board review findings”. He was cleared by Seyfarth Shaw of the most damaging allegations.
White is still the subject of an ASIC insider trading investigation probing the share sales of three other senior executives.
As investors weigh how artificial intelligence may reshape software economics, in February, WiseTech said it would cut up to 2000 jobs as part of what it described as a “deliberate AI transformation journey”. The stock now trades at four-year lows.
“Every business has something bad happen to it,” Gregg says. “What is important is if the fundamentals are sound.”
Staying through those periods, rather than exiting early, became central to his approach following his experience at HCN. Gregg highlights his sustained conviction in the fundamentals of his investment, suggesting “the effect of AI on sophisticated, integrated companies is overdone”.
Many systems, he argues, still rely on a level of “trust” that AI has yet to replicate. Even so, Gregg does see the environment shifting.
“Up until recently SaaS could be rock-solid forever,” he says. Now, investors are increasingly making “decisions based on externalities”.
At Shearwater Capital, the venture capital firm Gregg founded with Zavos and Gibbon, the same core philosophy he applied to his WiseTech investment persists, but the process has deepened.
The investment lens is consistent, identifying strong founders in markets that can sustain scale. “The problem has to be genuine and big enough” to enable a successful investment.
Founders remain central to Gregg’s current investments, but understanding them takes longer.
“In the early days we met the founder three or four times,” he says. Now, getting to know a founder is a months-long process. Nonetheless, they are “still looking for the same characteristics”.
He resists the idea that this is a filtering exercise. “It isn’t vetting. It is trying to understand, to be in alignment.” The objective is to “get to the essence of the founder”, an approach he links to a rule of thumb he once encountered; meeting someone multiple times, in different contexts, before forming a view.
That framework underpins investments such as Lyka, a subscription-based pet food company. The attraction again centres on people. The founders are “strong individuals” and “ambitious enough to execute”.
Shearwater invested in Lyka’s 2021 Series A funding round, and has further invested in 2023, 2025 and 2026. Today, Lyka generates about $200m in annual recurring revenue, with more than 100,000 dogs on its platform.
Shearwater is structured without a fixed investment horizon. Like Gregg’s WiseTech journey, the investors are “happy to stay on the journey for the long term”. The process of bringing in outside capital has recently commenced.
Gregg admits that working with start-up founders can be “tough,” but the approach is defined. Shearwater looks for founders “amenable to support” and aims to be “helpful and active, but not intrusive. Not telling them what to do”.
Often, the role of an angel investor is underpinned by availability. Gregg points to his investment in Zac Zavos’s company, now managing partner at Shearwater, who would call him daily.
“It’s a power to discuss things,” he says. “Less about profound insights and more about being there.”
He first met Zavos through the UNSW Cricket Club, a network that also introduced him to Atticus Fleming, now chief executive of the Great Southern Land Conservancy.
That conservancy has a central focus outside investing. Established in late 2024 with his wife Sue, it reflects a shift in how they think about capital.
“Investing gave us more wealth than we ever expected. We sat down and said we have a responsibility to do something meaningful.”
The model is direct. The conservancy is a charity that acquires land for protection and restoration and began with a 730ha property in northern New South Wales. It has now expanded to around 9000ha across five sites.
It is currently self-funded, supported by an initial $3m contribution from Gregg, with ambitions to scale over time.
The approach mirrors Shearwater in structure and intent, a long-term, patient and hands-on project. It includes “innovative land management such as drone surveys”.
Over time, Gregg hopes to broaden the funding base, but for now it remains a private effort.
Gregg’s advice for aspiring investors and entrepreneurs reflects the same orientation toward fundamentals.
He acknowledges there is a “seismic shift” under way. The response is not to chase themes, but to build capability. “Get expertise,” he says and, as an investor, “learn solid fundamentals”.
